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Round 1: The one who has superhuman strength while also having comparable skill to Ollie.

Round 2: Ollie is going to need both his explosive arrows and a way to remove Cap's shield from the equation to have a chance here. BTW, does Steve have his classic shield here, or the ones T'Challa gave him in Infinity War?

Oliver has superior durability and far superior skill to Cap. Cap has a strength advantage, but the two have comparable reaction speed.

By our standards; Oliver is absolutely superhuman. He routinely casually tosses around fully grown men with one arm, and takes absurd punishment(bloodlusted Mirakuru Slade in a flashback, and Roy when he was going berserk on the stuff(Roy specifically, casually punched through a shipping crate with his fist, something only Bucky with his arm would be able to do so easily), being stabbed in the hip and kicked off a mountain and landing near the bottom of said mountain on a stone sticking out of the side, with only flakes of snow to break his fall(and no, Kusunei did not bring him back from the dead, she outright stated that all she did was bandage him up, the rest was all him), etc).

He has cleared out entire hallways and rooms of people with mostly only the use of his h2h skill, having been trained by Slade, a variant of the League of Assassins fighting style, and from the League itself, he has taken guys down about as fast as Cap despite not being on a super steroid. The guy has absurd damage soak, arguably superior to Caps. And while not as strong, he can absolutely hurt Cap as he has shown to be far stronger than any normal human. Like Cap; he is pushing CBPH levels, he is essentially CWs Batman.

Round 2: Cap is going to dominate with his shield if they get up close, Oliver is good with his bow but that isn't going to cut it. If they keep it far, Oliver can repeatedly fire off his newer arrows(they shoot a bunch of explosions all over the place after fired) to through Cap off balance and eventually be overwhelmed. If Cap gets close, he wins. From afar; Oliver can pull it off. Could go either way.

Oliver is tougher, as I've pointed out. He has superior feats in soak, that's it. And he isn't so behind Cap in strength that he couldn't hurt him.

i haven't seen ollie do anything to get near a guy who can casually toss full grown men like they weighed nothing, kick more grown men unconscious with a single blow, hold a motorcycle with two women on it over his head with no sign of straining, throw another motorcycle over his head while moving, easily rip solid logs of wood like he was tearing through paper and temperately keep a helicopter from taking off.

as for durability, he's thrown hands with both bucky and BP, both of whom are as strong as he is. in fact, it took several shots from bucky's metal arm from a non resisting cap before he even started bleeding. also, he was able to resist being knocked out by a stun stick (?). keep in mind, those things can knock out a full grown man like crossbones on contact.

i haven't seen ollie do anything to get near a guy who can casually toss full grown men like they weighed nothing, kick more grown men unconscious with a single blow, hold a motorcycle with two women on it over his head with no sign of straining, throw another motorcycle over his head while moving, easily rip solid logs of wood like he was tearing through paper and temperately keep a helicopter from taking off.

as for durability, he's thrown hands with both bucky and BP, both of whom are as strong as he is. in fact, it took several shots from bucky's metal arm from a non resisting cap before he even started bleeding. also, he was able to resist being knocked out by a stun stick (?). keep in mind, those things can knock out a full grown man like crossbones on contact.

Okay, I just listed feats in my original posts that address this, like have you even read it? Oliver also casually tosses fully grown men around with one arm, we have seen it several times these past two seasons, and also kick and punch grown men unconscious with a single blow(have you even watched the show?). Since you, for some reason, ignored my previous post; I'll repost it here:

Oliver has superior durability and far superior skill to Cap. Cap has a strength advantage, but the two have comparable reaction speed.

By our standards; Oliver is absolutely superhuman. He routinely casually tosses around fully grown men with one arm, and takes absurd punishment(bloodlusted Mirakuru Slade in a flashback, and Roy when he was going berserk on the stuff(Roy specifically, casually punched through a shipping crate with his fist, something only Bucky with his arm would be able to do so easily), being stabbed in the hip and kicked off a mountain and landing near the bottom of said mountain on a stone sticking out of the side, with only flakes of snow to break his fall(and no, Kusunei did not bring him back from the dead, she outright stated that all she did was bandage him up, the rest was all him), etc).

He has cleared out entire hallways and rooms of people with mostly only the use of his h2h skill, having been trained by Slade, a variant of the League of Assassins fighting style, and from the League itself, he has taken guys down about as fast as Cap despite not being on a super steroid. The guy has absurd damage soak, arguably superior to Caps. And while not as strong, he can absolutely hurt Cap as he has shown to be far stronger than any normal human. Like Cap; he is pushing CBPH levels, he is essentially CWs Batman.

Round 2: Cap is going to dominate with his shield if they get up close, Oliver is good with his bow but that isn't going to cut it. If they keep it far, Oliver can repeatedly fire off his newer arrows(they shoot a bunch of explosions all over the place after fired) to through Cap off balance and eventually be overwhelmed. If Cap gets close, he wins. From afar; Oliver can pull it off. Could go either way.